Dimethylformamide → [(2,3-Dimethoxy-2-methylpropoxy)methyl]benzene

Participants

Reaction Steps

1-(Benzyloxymethyl)-1-methylethane-1,2-diol (10 g) and sodium hydride (1.2 g) were stirred together in dimethyl formamide (50 ml) for 12 h; the reaction mixture was then treated with methyl iodide (7.1g) and again stirred for 4 h. The reaction product was then stripped at 100°/1 mm and the residue purified by chromatography on silica gel eluted with 9/1 methylene chloride/ether to give a small forerun of 1,2-dimethoxy-2-methyl-3-benzyloxypropane and then 11 g 1-methoxy-3-benzyloxy-2-methylpropan-2-ol as a colourless oil. The structure was confirmed by n.m.r. techniques.

Provenance & Evidence